JP2009292808A - Use of alkyl glycoside or mixture of at least two alkyl glycosides as agent for inhibiting microbe proliferation, and composition containing alkyl glycoside - Google Patents
Use of alkyl glycoside or mixture of at least two alkyl glycosides as agent for inhibiting microbe proliferation, and composition containing alkyl glycoside Download PDFInfo
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- JP2009292808A JP2009292808A JP2009090360A JP2009090360A JP2009292808A JP 2009292808 A JP2009292808 A JP 2009292808A JP 2009090360 A JP2009090360 A JP 2009090360A JP 2009090360 A JP2009090360 A JP 2009090360A JP 2009292808 A JP2009292808 A JP 2009292808A
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- Prior art keywords
- mixture
- agent
- alkyl
- dodecyl
- series
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- -1 alkyl glycoside Chemical class 0.000 title claims abstract description 82
- 229930182470 glycoside Natural products 0.000 title claims abstract description 64
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- 230000035755 proliferation Effects 0.000 title abstract 2
- 235000000346 sugar Nutrition 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
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- 230000012010 growth Effects 0.000 claims description 19
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Abstract
Description
本発明は、抗微生物特性を有するアルキルグリコシド及びアルキルグリコシド混合物の新規な使用及び前記アルキルグリコシドを含む組成物、特に化粧品、医薬又は食品組成物に関する。
[関連技術]
The present invention relates to a novel use of alkyl glycosides and alkyl glycoside mixtures having antimicrobial properties and compositions comprising said alkyl glycosides, in particular cosmetic, pharmaceutical or food compositions.
[Related technologies]
アルキルグリコシド及びそれらの用途は、特に米国特許出願公開第2006/0046969号明細書及び国際公開第2006/107386号パンフレットにより知られている。 Alkyl glycosides and their uses are known in particular from US 2006/0046969 and WO 2006/107386.
米国特許出願公開第2006/0046969号明細書には、少なくとも1種のアルキルグリコシド、少なくとも1種の糖及び少なくとも1種の治療剤を含む抗微生物性組成物が開示されている。 US 2006/0046969 discloses an antimicrobial composition comprising at least one alkyl glycoside, at least one sugar and at least one therapeutic agent.
国際公開第2006/107386号パンフレットには、式(Z)n−O−R(式中、Zは糖であり、Rは8〜30個の炭素原子を含む一般に直鎖状のアルキル基である)のアルキルグリコシドであってよい非イオン性界面活性剤を含む膣感染症を抑制及び/又は治療するための組成物が開示されている。 In WO 2006/107386, the formula (Z) n —O—R, wherein Z is a sugar and R is a generally linear alkyl group containing 8 to 30 carbon atoms. A composition for inhibiting and / or treating vaginal infections comprising a nonionic surfactant, which may be an alkyl glycoside.
しかし、本出願人は、この化学ファミリーの化合物の抗微生物用途への能力を高めることを追求してきた。
[本発明の目的]
However, Applicants have sought to enhance the ability of this chemical family of compounds for antimicrobial applications.
[Object of the present invention]
したがって、本発明の1つの主な目的は、特に化粧品、医薬又は食品組成物中で、微生物の増殖を阻止するための新規な剤を提供することである。 Accordingly, one main object of the present invention is to provide a novel agent for inhibiting the growth of microorganisms, especially in cosmetic, pharmaceutical or food compositions.
本発明の1つの主な目的はまた、組成物、特に化粧品、医薬又は食品組成物に用いられ得る、微生物の増殖を阻止するための新規な剤を提供することであり、その利点は、これと同じ機能を有し、組成物、特に化粧品、医薬又は食品組成物の処方で従来から使用されている他の剤又は剤の混合物を置き換えることが想定できることである。本発明は特に、体若しくは顔の皮膚又は表面身体生長物(superficial body growth)に適用されるように特に意図された組成物において、毒性があるとされているパラベン族のいかなる防腐剤の使用をも避け、且つ本発明のアルキルグリコシドなどの非毒性であり、微生物に対して防腐剤と同等の効果を有する生成物によってこれらの組成物を保護する可能性を提供する。 One main object of the present invention is also to provide a novel agent for inhibiting the growth of microorganisms which can be used in compositions, in particular cosmetic, pharmaceutical or food compositions, the advantages of which are Can be envisaged to replace other agents or mixtures of agents conventionally used in the formulation of compositions, in particular cosmetic, pharmaceutical or food compositions. The present invention particularly relates to the use of any paraben preservatives that are said to be toxic, especially in compositions intended to be applied to body or facial skin or superficial body growth. And offers the possibility of protecting these compositions with products that are non-toxic, such as the alkyl glycosides of the present invention, and have an effect equivalent to preservatives against microorganisms.
本発明の目的は、最後に、簡単で費用がかからず、工業用及び化粧品用のスケールで用いることができる解決策によって技術的課題を解決することでもある。
[発明の説明]
The aim of the invention is also finally to solve the technical problem by means of a solution that is simple and inexpensive and can be used on industrial and cosmetic scales.
[Description of the Invention]
本発明の第1の主題は、特に化粧品、医薬又は食品組成物における、微生物の増殖を阻止するための剤としてのアルキルグリコシド又は少なくとも2種のアルキルグリコシドの混合物の新規な使用に関し、アルキルグリコシド又は前記混合物のアルキルグリコシドは、一般式(S)−O−R(式中、(S)は1個の糖単位又は一連の2〜8個の同一若しくは異なる糖単位で形成されるオリゴ糖であり、前記糖単位はペントース又はヘキソース型の還元糖又はこれらの糖の誘導体であり、Rは1〜24個の炭素原子を含むアルキル基である)を有することを特徴とする。 The first subject of the present invention relates to the novel use of alkyl glycosides or mixtures of at least two alkyl glycosides as agents for inhibiting the growth of microorganisms, especially in cosmetic, pharmaceutical or food compositions. The alkyl glycoside of the mixture is a general formula (S) -O-R, wherein (S) is an oligosaccharide formed with one sugar unit or a series of 2-8 identical or different sugar units. The sugar unit is a pentose or hexose-type reducing sugar or a derivative of these sugars, and R is an alkyl group containing 1 to 24 carbon atoms).
特に好ましい変形形態によれば、アルキルグリコシドは、一般式(I)(S1)−O−R1(式中、(S1)はデオキシアルドヘキソースであり、R1は1〜24個の炭素原子を有するアルキル基である)の化合物から選択され、或いは According to a particularly preferred variant, the alkyl glycoside is of the general formula (I) (S 1 ) —O—R 1 , where (S 1 ) is deoxyaldohexose and R 1 is 1 to 24 carbons. Or an alkyl group having an atom), or
少なくとも2種のアルキルグリコシドの混合物は、
− 上記定義の一般式(I)の化合物から選択される少なくとも1種の化合物を含む混合物、
− 一般式(II)(S2)−O−R2(式中、(S2)は1個の糖単位又は一連の2〜8個の同一若しくは異なる糖単位で形成されるオリゴ糖であり、(R2)は1〜6個の炭素原子を有するアルキル基である)の化合物から選択される少なくとも1種の化合物、及び一般式(III)(S3)−O−R3(式中、(S3)は糖単位又は一連の2〜8個の同一若しくは異なる糖単位で形成されるオリゴ糖であり、R3は8〜24個の炭素原子を有するアルキル基である)の化合物から選択される少なくとも1種の化合物を含む混合物
から選択される。
A mixture of at least two alkyl glycosides is
A mixture comprising at least one compound selected from the compounds of general formula (I) as defined above,
The general formula (II) (S 2 ) —O—R 2 , wherein (S 2 ) is an oligosaccharide formed with one sugar unit or a series of 2-8 identical or different sugar units , (R 2) at least one compound selected from the compounds of an alkyl group) having 1 to 6 carbon atoms, and the general formula (III) (S 3) -O -R 3 ( wherein , (S 3 ) is a saccharide unit or a series of 2 to 8 identical or different saccharide units and an oligosaccharide formed of R 3 is an alkyl group having 8 to 24 carbon atoms) Selected from a mixture comprising at least one selected compound.
本発明はまた、特にこれらが微生物増殖阻止に有効な濃度で存在する化粧品、医薬又は食品組成物における、本発明による化合物の及び混合物の新規な使用に関する。 The invention also relates to a novel use of the compounds and mixtures according to the invention, in particular in cosmetic, pharmaceutical or food compositions where they are present in a concentration effective to inhibit microbial growth.
本発明は特に、グリコシド基がデオキシアルドヘキソースであるアルキルグリコシドに関する。デオキシアルドヘキソースは6個の炭素原子からなる糖(ヘキソース)で、その水酸基の1個又は複数が水素原子で置換されている。デオキシアルドヘキソースには、フコース、ラムノース、キノボース又はニューモース(Pneumose)を挙げることができる。 The invention particularly relates to alkyl glycosides in which the glycoside group is deoxyaldohexose. Deoxyaldohexose is a sugar (hexose) consisting of 6 carbon atoms, and one or more of its hydroxyl groups are replaced with hydrogen atoms. Deoxyaldohexose can include fucose, rhamnose, quinobose, or pneumose.
本発明はまた、特に、アルキル鎖が異なる長さを有し、これらの混合物の効果を個別に試験した化合物について得られた結果と比較した際に相乗効果を与えるアルキルグリコシドの混合物に関する。 The invention also relates in particular to mixtures of alkyl glycosides in which the alkyl chains have different lengths and give a synergistic effect when comparing the effects of these mixtures with the results obtained for the compounds tested individually.
アルキルグリコシドはその両新媒性の性質により、種々の細菌、真菌又は酵母に対して活性を示すことが知られているが、本発明は、その活性スペクトルがその構造によって変化することを示す。したがって、グリコシド基がデオキシアルドヘキソースであるアルキルグリコシドの具体的な使用によって、これらの化合物の注目すべき抗微生物特性、及びしたがって防腐性を実証することが可能になる。さらに、混合物中に異なる構造のアルキルグリコシドを組み合わせることによって、細菌、真菌及び酵母型の多くの病原性微生物に対する相補的な又は相乗的でさえもある活性を得ることができる。 Alkyl glycosides are known to be active against various bacteria, fungi or yeasts due to their amphoteric nature, but the present invention shows that their activity spectrum varies with their structure. Thus, the specific use of alkyl glycosides in which the glycoside group is deoxyaldohexose makes it possible to demonstrate the remarkable antimicrobial properties and thus antiseptic properties of these compounds. Furthermore, by combining differently structured alkyl glycosides in the mixture, it is possible to obtain complementary or even synergistic activity against many pathogenic microorganisms of bacterial, fungal and yeast type.
本発明によれば、R及び/又はR1及び/又はR2及び/又はR3基は、飽和アルキル基、好ましくは飽和直鎖状アルキル基であってよい。 According to the invention, the R and / or R 1 and / or R 2 and / or R 3 groups may be saturated alkyl groups, preferably saturated linear alkyl groups.
特に、R及び/又はR1及び/又はR3基は、好ましくは8〜16個の炭素原子を含むアルキル基であり、特に好ましくはドデシル基である。R及び/又はR2基は、特に好ましくはメチル基である。 In particular, the R and / or R 1 and / or R 3 groups are preferably alkyl groups containing 8 to 16 carbon atoms, particularly preferably dodecyl groups. The R and / or R 2 group is particularly preferably a methyl group.
本発明によれば、デオキシアルドヘキソース基(S1)は、左旋性糖系列(L系列)又は右旋性糖系列(D系列)から等しく良好に選択できるが、より特に左旋性糖から選択される。 According to the present invention, the deoxyaldohexose group (S 1 ) can be equally well selected from the levorotary sugar series (L series) or the dextrorotatory sugar series (D series), but more particularly selected from levorotatory sugars. The
本発明によるアルキルグリコシドの合成条件によって、糖単位又はオリゴ糖(S)とR基との結合がα型又はβ型のいずれか一方の化合物を特に得ることが可能であり、或いはその一部分がこのα型結合を有し、その結果生じた部分が同じβ型結合を有する同じ化合物の混合物に到達することも可能である。 Depending on the synthesis conditions of the alkylglycoside according to the present invention, it is possible to obtain a compound in which the linkage between the sugar unit or oligosaccharide (S) and the R group is either α-type or β-type, or a part thereof It is also possible to have a mixture of the same compound with an α-type bond and the resulting part having the same β-type bond.
本発明によれば、オリゴ糖(S)とR基との結合は、等しく良好にα型又はβ型であってよいが、好ましくはβ型である。 According to the present invention, the linkage between the oligosaccharide (S) and the R group may be equally well α-type or β-type, but is preferably β-type.
特に、デオキシアルドヘキソース(S1)とアルキル基R1との結合は、等しく良好にα型又はβ型であってよいが、好ましくはβ型である。 In particular, the bond between deoxyaldohexose (S 1 ) and alkyl group R 1 may be equally well α-type or β-type, but is preferably β-type.
デオキシアルドヘキソース基は、好ましくはフコース又はラムノースから選択される。 The deoxyaldhexose group is preferably selected from fucose or rhamnose.
好ましい実施形態によると、デオキシアルドヘキソース基は、β−L−フコース及びβ−L−ラムノースから選択される。 According to a preferred embodiment, the deoxyaldhexose group is selected from β-L-fucose and β-L-rhamnose.
したがって、本発明で用いられるアルキルグリコシドは、より特にドデシルL−フコシド及びドデシルL−ラムノシドから選択される。 Thus, the alkyl glycoside used in the present invention is more particularly selected from dodecyl L-fucoside and dodecyl L-rhamnoside.
本発明によれば、第1の態様において、(S)及び/又は(S2)及び/又は(S3)基は、1個の糖単位又は一連の2個の糖単位(二糖類)若しくは3個の糖単位(三糖類)で形成されたオリゴ糖であってよい。 According to the present invention, in the first aspect, the (S) and / or (S 2 ) and / or (S 3 ) groups are one sugar unit or a series of two sugar units (disaccharides) or It may be an oligosaccharide formed from three sugar units (trisaccharides).
本発明によれば、糖単位は、より特に、右旋性糖系列(D系列)から選択される。 According to the invention, the sugar unit is more particularly selected from the dextrorotatory sugar series (D series).
好ましい実施形態によれば、糖単位は、ペントース又はヘキソース型の還元糖又はこれらの糖の誘導体、好ましくはウロン酸誘導体、硫酸誘導体又はデオキシ誘導体である。 According to a preferred embodiment, the sugar unit is a pentose or hexose type reducing sugar or a derivative of these sugars, preferably a uronic acid derivative, a sulfuric acid derivative or a deoxy derivative.
別の好ましい実施形態によれば、糖単位は、アラビノース、キシロース、リボース、グルコース、ガラクトース、マンノース、ラムノース、フコースから選択される。 According to another preferred embodiment, the sugar unit is selected from arabinose, xylose, ribose, glucose, galactose, mannose, rhamnose, fucose.
別の特に好ましい実施形態によれば、選択される糖単位はD−グルコースである。 According to another particularly preferred embodiment, the selected sugar unit is D-glucose.
本発明によれば、第2の態様において、(S)及び/又は(S2)及び/又は(S3)基は、一連の2〜8個の糖単位で形成されるオリゴ糖である。 According to the present invention, in a second aspect, the (S) and / or (S 2 ) and / or (S 3 ) groups are oligosaccharides formed with a series of 2-8 saccharide units.
オリゴ糖を形成する一連の糖単位は、同一の糖単位の繰り返しから形成されてもよく、異なる糖単位から形成されてもよい。 The series of saccharide units forming the oligosaccharide may be formed from repetition of the same saccharide unit or may be formed from different saccharide units.
オリゴ糖を形成する一連の糖単位は、直鎖状でも分枝状でもよい。 The series of sugar units forming the oligosaccharide may be linear or branched.
糖単位間の結合は、糖のヘミアセタール炭素(アノマー炭素、1番)のアルコール官能基の還元性基(水酸基)と、別の分子の酸基(遊離水素)との共有グリコシド結合によって形成される。 The linkage between sugar units is formed by a covalent glycosidic bond between the reducing group (hydroxyl group) of the alcohol functional group of the hemiacetal carbon (anomeric carbon, No. 1) of the sugar and the acid group (free hydrogen) of another molecule. The
この結合は等しく良好にα又はβ型であってよいが、好ましくはβ型である。 This bond may be equally well α or β type, but is preferably β type.
グリコシド結合は1−3型、すなわち第1の糖の1番のアノマー炭素と第2の糖の3番の炭素の水酸基との結合、1−4型又は1−6型であってよい。
The glycosidic bond may be of the 1-3 type, i.e., the bond between the
結合は好ましくは1−4型である。 The bond is preferably of the 1-4 type.
好ましい実施形態によれば、オリゴ糖は、マルトース、セロビオース、ラクトース、フルクトース、マルトトリオース、セロトリオースから選択できる。 According to a preferred embodiment, the oligosaccharide can be selected from maltose, cellobiose, lactose, fructose, maltotriose, cellotriose.
オリゴ糖は、左旋性(L−)又は右旋性(D−)であってよく、好ましくは(D−)系列のオリゴ糖から選択される。 The oligosaccharide may be levorotatory (L-) or dextrorotatory (D-) and is preferably selected from the (D-) series of oligosaccharides.
別の好ましい実施形態によれば、オリゴ糖は、β−D−マルトース又はβ−D−マルトトリオースから選択される。 According to another preferred embodiment, the oligosaccharide is selected from β-D-maltose or β-D-maltotriose.
本発明によれば、使用されるアルキルグリコシドの少なくとも1種は、ドデシルβ−L−ラムノシド、ドデシルβ−L−フコシド、メチルβ−D−マルトシド、メチルβ−D−マルトトリオシド、ドデシルβ−D−マルトシド、ドデシルβ−D−マルトトリオシドから選択できる。 According to the invention, at least one of the alkyl glycosides used is dodecyl β-L-rhamnoside, dodecyl β-L-fucoside, methyl β-D-maltoside, methyl β-D-maltotrioside, dodecyl β- It can be selected from D-maltoside and dodecyl β-D-maltotrioside.
第1の好ましい変形形態においては、混合物中に1/99〜99/1、好ましくは75/25〜25/75、より好ましくは約50/50の比で存在する2種のアルキルグリコシドからなる混合物が使用される。 In a first preferred variant, a mixture of two alkyl glycosides present in the mixture in a ratio of 1/99 to 99/1, preferably 75/25 to 25/75, more preferably about 50/50. Is used.
第1の好ましい混合物は、メチルβ−D−マルトシドと一連の3個の糖単位で形成されるアルキルグリコシド、好ましくはドデシルβ−D−マルトトリオシドとによって形成される。 The first preferred mixture is formed by methyl β-D-maltoside and an alkyl glycoside formed by a series of three sugar units, preferably dodecyl β-D-maltotrioside.
別の好ましい混合物は、メチルβ−D−マルトトリオシドと一連の2個の糖単位で形成されるアルキルグリコシド、好ましくはドデシルβ−D−マルトシドとによって形成される。 Another preferred mixture is formed by methyl β-D-maltotrioside and an alkyl glycoside formed by a series of two sugar units, preferably dodecyl β-D-maltoside.
特に、好ましい混合物は、ドデシルβ−D−マルトトリオシドを含むことを特徴とする一組の2種のアルキルグリコシドの組によって形成される。 In particular, a preferred mixture is formed by a set of two alkyl glycosides characterized by comprising dodecyl β-D-maltotrioside.
本実施形態によれば、特に好ましい混合物は、ドデシルβ−D−マルトトリオシドとメチルβ−D−マルトシドとによって形成される混合物である。 According to this embodiment, a particularly preferred mixture is a mixture formed by dodecyl β-D-maltotrioside and methyl β-D-maltoside.
第2の好ましい変形形態においては、4種のアルキルグリコシドからなるアルキルグリコシドの混合物が用いられる。 In a second preferred variant, a mixture of alkyl glycosides consisting of four alkyl glycosides is used.
好ましくは、4種のアルキルグリコシドは、実質的に等しい比率で混合物中に存在する。 Preferably, the four alkyl glycosides are present in the mixture in substantially equal proportions.
特に、好ましい混合物は、メチルβ−D−マルトシド、メチルβ−D−マルトトリオシド、ドデシルβ−D−マルトシド、ドデシルβ−D−マルトトリオシドによって形成される。 Particularly preferred mixtures are formed by methyl β-D-maltoside, methyl β-D-maltotrioside, dodecyl β-D-maltoside, dodecyl β-D-maltotrioside.
一般に、本発明による混合物の場合には、異なる糖基又はデオキシ糖基及び/又は実質的に異なる長さのアルキル基を有するアルキルグリコシドを組み合わせるのが特に好ましい。 In general, in the case of the mixtures according to the invention, it is particularly preferred to combine alkyl glycosides having different sugar groups or deoxy sugar groups and / or alkyl groups of substantially different lengths.
これにより、化合物の構造による微生物の感受性の相違によって、より広いスペクトルをカバーすることが可能になる。 This makes it possible to cover a wider spectrum due to the difference in susceptibility of microorganisms depending on the structure of the compound.
最後に、本発明によるアルキルグリコシド又はアルキルグリコシドの混合物は、組成物、特に化粧品、医薬又は食品組成物の保存と細菌学的安定性を可能にするような抗微生物効果を提供するのに充分な量で用いられる。 Finally, the alkyl glycosides or mixtures of alkyl glycosides according to the invention are sufficient to provide an antimicrobial effect that allows the storage and bacteriological stability of the composition, in particular a cosmetic, pharmaceutical or food composition. Used in quantity.
本発明によれば、微生物増殖阻止剤は、微生物増殖阻止剤を含む組成物に対して、好ましくは0.001重量%〜10重量%、前記組成物に対して特に0.01重量%〜5重量%の量で存在する。 According to the invention, the microbial growth inhibitor is preferably from 0.001% to 10% by weight, in particular from 0.01% to 5%, based on the composition comprising the microbial growth inhibitor. Present in an amount by weight.
したがって、本発明によるそのような混合物は、他のいかなる防腐剤もなしに、化粧品用又は医薬品用組成物の調製を可能にする。 Thus, such mixtures according to the invention allow the preparation of cosmetic or pharmaceutical compositions without any other preservatives.
本発明の第2の主題は、化粧品、医薬品又は食品用組成物に関し、組成物が、特に微生物増殖阻止剤として、
− 一般式(I)(S1)−O−R1(式中、(S1)はデオキシアルドヘキソースであり、R1は1〜24個の炭素原子を含むアルキル基である)の化合物から選択される少なくとも1種の化合物を含む混合物、
− 一般式(II)(S2)−O−R2(式中、(S2)は1個の糖単位又は一連の2〜8個の同一若しくは異なる糖単位で形成されるオリゴ糖であり、(R2)は1〜6個の炭素原子を含むアルキル基である)の化合物から選択される少なくとも1種の化合物及び一般式(III)(S3)−O−R3(式中、(S3)は1個の糖単位又は一連の2〜8個の同一若しくは異なる糖単位で形成されるオリゴ糖であり、R3は8〜24個の炭素原子を含むアルキル基である)の化合物から選択される少なくとも1種の化合物を含む混合物
から選択される少なくとも2種のアルキルグリコシドの混合物を含むことを特徴とする、化粧品、医薬又は食品組成物に関する。
The second subject of the present invention relates to a cosmetic, pharmaceutical or food composition, wherein the composition, in particular as a microbial growth inhibitor,
A compound of the general formula (I) (S 1 ) —O—R 1 , wherein (S 1 ) is deoxyaldohexose and R 1 is an alkyl group containing 1 to 24 carbon atoms A mixture comprising at least one selected compound;
The general formula (II) (S 2 ) —O—R 2 , wherein (S 2 ) is an oligosaccharide formed with one sugar unit or a series of 2-8 identical or different sugar units , (R 2) at least one compound the general formula (III) (S 3) -O -R 3 ( wherein selected from the compounds of the alkyl is group) containing 1 to 6 carbon atoms, (S 3 ) is an oligosaccharide formed from one saccharide unit or a series of 2 to 8 identical or different saccharide units, and R 3 is an alkyl group containing 8 to 24 carbon atoms) It relates to a cosmetic, pharmaceutical or food composition characterized in that it comprises a mixture of at least two alkyl glycosides selected from a mixture comprising at least one compound selected from compounds.
本発明によれば、上記混合物は特に、本発明の第1の主題に関する前述の考察で定義されるものである。 According to the present invention, the above mixture is in particular as defined in the above discussion regarding the first subject matter of the present invention.
本発明によれば、組成物は、さらに好ましくは、少なくとも1種の化粧品用又は医薬品用活性剤及び少なくとも1種の化粧品又は医薬として許容される賦形剤を含む。 According to the invention, the composition further preferably comprises at least one cosmetic or pharmaceutically active agent and at least one cosmetic or pharmaceutically acceptable excipient.
化粧品組成物は、等しく良好に皮膚若しくは表面身体生長物用のケア用品、メークアップ用品或いはシャンプー、クレンジング又は皮膚若しくは表面身体生長物用のメークアップ除去用品などのヘルスケア用品であってよい。 The cosmetic composition may equally well be a health care product such as a care product for skin or surface body growth, a makeup product or a shampoo, cleansing or makeup removal product for skin or surface body growth.
好ましい実施形態によれば、組成物は、顔若しくは体の皮膚の全部若しくは一部又は表面身体生長物に適用されることが意図されている。 According to a preferred embodiment, the composition is intended to be applied to all or part of the skin of the face or body or surface body growth.
特に、前記組成物は、セラム、ローション、エマルジョン、好ましくはケアクリーム、ヒドロゲル、好ましくはマスク、マスカラ、ファンデーション、アイシャドウ、アイライナーであってよく、又はスティックの形態で提供され得る。 In particular, the composition may be a serum, lotion, emulsion, preferably a care cream, hydrogel, preferably a mask, mascara, foundation, eye shadow, eyeliner, or may be provided in the form of a stick.
化粧品用活性剤は、たとえば、皮膚美白化活性を有する物質、痩身活性を有する物質から得られる物質、湿潤化活性を有する物質、鎮静化、緩和又は弛緩活性を有する物質、肌色の輝きを強化するために皮膚の微小循環を刺激する活性を有する物質、脂性皮膚の手入れのための脂漏調節活性を有する物質、皮膚を洗浄又は皮膚から汚れを取り除くことを意図した物質、抗フリーラジカル活性を有する物質、皮膚の老化の影響を弱める又は遅延させることを意図した物質から選択される化合物であってよい。 Cosmetic active agents, for example, substances that have a skin lightening activity, substances obtained from substances having a slimming activity, substances that have a moistening activity, substances that have a sedative, relaxation or relaxation activity, enhance skin color shine Substances that have the activity of stimulating the microcirculation of the skin, substances that have seborrhea regulating activity for the care of oily skin, substances that are intended to clean or remove dirt from the skin, have anti-free radical activity It may be a compound selected from substances intended to attenuate or delay the effects of skin aging.
化粧品に受容できる賦形剤は、顔料、着色剤、ポリマー、界面活性剤、レオロジー促進剤、香料、電解質、pH調整剤、抗酸化剤、防腐剤、及びこれらの混合物を含む群から選択できる。 The cosmetically acceptable excipient can be selected from the group comprising pigments, colorants, polymers, surfactants, rheology promoters, fragrances, electrolytes, pH adjusters, antioxidants, preservatives, and mixtures thereof.
本発明によれば、組成物は、上記混合物を好ましくは0.001重量%〜10重量%、特に0.01重量%〜5重量%含む。 According to the invention, the composition preferably comprises 0.001% to 10% by weight, in particular 0.01% to 5% by weight, of the above mixture.
本発明に従って定義されるアルキルグリコシド又は少なくとも2種のアルキルグリコシドの混合物は、特に化粧品、医薬又は食品組成物において、細菌、真菌又は酵母型の微生物の増殖を回避することによって組成物の微生物学的安定性を確実にするために有効な量で用いられる。 Alkyl glycosides or mixtures of at least two alkyl glycosides defined according to the present invention can be used to prevent the growth of bacterial, fungal or yeast type microorganisms, especially in cosmetic, pharmaceutical or food compositions. Used in an effective amount to ensure stability.
したがって、本発明によるアルキルグリコシドのそのような混合物を含む組成物は、微生物の増殖を阻止するための他の剤、特にパラベン族の化合物を全く含まないことが可能である。 Thus, a composition comprising such a mixture of alkyl glycosides according to the invention can be free of any other agent for inhibiting the growth of microorganisms, in particular paraben group compounds.
本発明の他の目的、特徴及び利点は、以下の説明的記述に照らして明確に現れるであろう。この記述は説明の目的のみで与えられる本発明の種々の典型的な実施形態を参照してなされるもので、したがって決して本発明の範囲を限定するものではない。実施例においては、特記しない限り、すべての百分率は重量基準であり、温度は度(摂氏)であり、圧力は大気圧である。 Other objects, features and advantages of the present invention will appear clearly in light of the following descriptive description. This description is made with reference to various exemplary embodiments of the invention which are given for the purpose of illustration only, and thus are not intended to limit the scope of the invention in any way. In the examples, unless otherwise specified, all percentages are by weight, temperatures are in degrees (Celsius), and pressure is atmospheric pressure.
材料及び方法
1.化合物の合成
特記しない限り、種々のアルキルグリコシドは、Takeoらによって記載された方法に従って合成される(Carbohydrate Research、48(1976)197〜208頁)。
Materials and Methods Synthesis of Compounds Unless otherwise stated, various alkyl glycosides are synthesized according to the method described by Takeo et al. (Carbohydrate Research 48 (1976) 197-208).
ここで用いる合成方法はグリコシル化ステップ(アルキル鎖のグラフト)のみにおいてその出版物と異なり、ここではベンゼンをジクロロメタン(CH2Cl2)で置き換え、酢酸水銀をHgO/HgBR2の混合物で置き換える。このステップは下に例示する化合物のそれぞれについて具体的に記載される。 The synthetic method used here differs from that publication only in the glycosylation step (alkyl chain grafting), where benzene is replaced with dichloromethane (CH 2 Cl 2 ) and mercury acetate is replaced with a mixture of HgO / HgBR 2 . This step is specifically described for each of the compounds exemplified below.
充分な収率をもって反応を完結させるための反応用の化合物、触媒及び反応条件の選択は、当技術分野においてよく知られている。 The selection of reaction compounds, catalysts and reaction conditions to complete the reaction with sufficient yield is well known in the art.
次に試験するために合成する生成物は下記の通りである。
Rha−1:メチルL−ラムノシド、実施例1に従って調製
Rha−8:オクチルL−ラムノシド
Rha−12:ドデシルL−ラムノシド
Fuc−8:オクチルβ−L−フコシド、実施例2に従って調製
Fuc−12:ドデシルβ−L−フコシド
DP2−1:メチルβ−D−マルトシド、実施例4に従って調製
DP2−12:ドデシルβ−D−マルトシド、ACROS ORGANICS由来
DP3−1:メチルβ−D−マルトリオシド、実施例5に従って調製
DP3−12:ドデシルβ−D−マルトトリオシド、実施例6に従って調製
The products synthesized for the next test are as follows.
Rha-1: methyl L-rhamnoside, prepared according to example 1 Rha-8: octyl L-rhamnoside Rha-12: dodecyl L-rhamnoside Fuc-8: octyl β-L-fucoside, prepared according to example 2 Fuc-12: Dodecyl β-L-fucoside DP2-1: methyl β-D-maltoside, prepared according to Example 4 DP2-12: dodecyl β-D-maltoside, derived from ACROS ORGANICS DP3-1: methyl β-D-maltrioside, Example 5 Prepared according to DP3-12: dodecyl β-D-maltotrioside, prepared according to Example 6
2.アルキルグリコシドの及びアルキルグリコシドの混合物の抗微生物活性測定試験
a)試験の原理
予め試験菌株を接種したpH6、pH7及びpH8の培地を、1ディッシュについて1pH及び1菌株となるよう、ペトリディッシュに注ぐ。
固化後に、試験物質の各濃度並びに溶媒対照及び陽性対照について、100μlが沈殿する。
培養後、試験生成物を寒天内に拡散させた後に阻止用直径を測定し、それにより微生物の増殖を阻止する生成物の最低濃度である最小静菌濃度(MIC)を推定する。
2. Antimicrobial Activity Measurement Test of Alkyl Glycosides and Mixtures of Alkyl Glycosides a) Principle of Test Pour dish of pH 6, pH 7 and
After solidification, 100 μl is precipitated for each concentration of test substance and for solvent and positive controls.
After culturing, the test product is allowed to diffuse into the agar and then the blocking diameter is measured, thereby estimating the minimum bacteriostatic concentration (MIC), which is the lowest concentration of product that inhibits microbial growth.
b)材料及び方法
材料
− 麦角菌入り滅菌済み直径90mmペトリディッシュ、
− ノギス、
− 滅菌済み鋼製シリンダー。
培地
− 寒天培地B:大豆及びカゼインペプトン含有寒天培地、
− 寒天培地C:クロロアムフェニコール含有サブロー−グルコース−寒天培地、
− トリプトン塩、
− 糸状菌用希釈剤、
− 緩衝NaCl、
− ミュラー−ヒントン培地、pH7。
試薬
− 滅菌水、
− メタノール、
− KATHON(登録商標)(Rohm & Haas由来)。
菌株
試験用菌株は下記の通りである。
− Aspergillus niger IP 1431.83、
− Candida albicans IP 48.72、
− Enterococcus hirae CIP 58.55
− Staphylococcus aureus CIP 4.83、
− Burkholderia cepacia CIP 103924、
− Pseudomonas aeruginosa CIP 82.1118。
b) Materials and methods
Materials- Sterilized 90mm diameter petri dish with ergot bacteria,
-Calipers,
-Sterilized steel cylinder.
Medium -Agar medium B: Agar medium containing soybean and casein peptone,
-Agar medium C: chloroamphenicol-containing Sabouraud-glucose-agar medium,
-Tryptone salt,
-Diluent for filamentous fungi,
-Buffered NaCl,
-Mueller-Hinton medium, pH 7.
Reagents -sterile water,
-Methanol,
-KATHON® (from Rohm & Haas).
Strains The test strains are as follows.
-Aspergillus niger IP 1431.83,
-Candida albicans IP 48.72,
-Enterococcus hirae CIP 58.55
-Staphylococcus aureus CIP 4.83,
-Burkholderia cepacia CIP 103924,
-Pseudomonas aeruginosa CIP 82.1118.
c)培地の接種
それぞれの菌株に対し、pH6、pH7及びpH8の3種のミュラー−ヒントン培地各120mlが、107CFU/mlのタイターを有する各微生物懸濁液1.2mlに接種され、105CFU/mlに等しいタイターを得る。
1培地及び1菌株について1ディッシュを用い、各ディッシュに15mlを加えて、固化後、各ディッシュの表面に3個の鋼製シリンダーを乗せる。
試験生成物濃度範囲の調製
試験用アルキルグリコシドからなる粉末100mg(およそ)をメタノール1mlに取る(10%溶液A)。
次に、下記のように濃度範囲を調製する。
− 1%溶液B1:溶液A 300μl+滅菌水2.7ml、
− 0.5%溶液B2:溶液A 300μl+滅菌水5.7ml、
− 0.1%溶液B3:溶液B1 1ml+滅菌水9ml、
− 0.05%溶液B4:溶液B2 1ml+滅菌水9ml。
試験の間、溶液B2、B3及びB4のみを試験する。
溶媒対照の調製
滅菌水中でメタノールの1/10希釈液を調製する。
試験溶液の付置及び培養
下記の溶液100μl(pH6、pH7及びpH8)を各シリンダーに加える。
− メタノール対照(pH7でそれぞれの菌株について調製)
− 0.05%溶液B4、
− 0.1%溶液B3、
− 0.5%溶液B2。
37℃±1℃で24時間培養(Enterococcus hiraeについては48時間)。
最小阻止濃度(MIC)の決定
試験生成物を寒天内に拡散させた後、微生物増殖阻止の結果としての阻止用直径の測定を、ノギスを用いてmm単位で行う。
最小静菌濃度(MIC)は、微生物の増殖を阻止する生成物の最低濃度として与えられる。
最高濃度(500μm/ml)が不活性の場合には、これを記録する(>500)。
c) Inoculation of medium For each strain, 120 ml of each of the three Mueller-Hinton mediums at pH 6, pH 7 and
One dish is used for one medium and one strain, 15 ml is added to each dish, and after solidification, three steel cylinders are placed on the surface of each dish.
Take 100 mg (approximately) of the powder consisting of the alkylglycoside for preparation test in the test product concentration range in 1 ml of methanol (10% solution A).
Next, the concentration range is prepared as follows.
-1% solution B1: 300 μl of solution A + 2.7 ml of sterile water,
-0.5% solution B2: 300 μl of solution A + 5.7 ml of sterile water,
-0.1% solution B3: 1 ml of solution B1 + 9 ml of sterilized water,
-0.05% solution B4: 1 ml of solution B2 + 9 ml of sterile water.
During the test, only solutions B2, B3 and B4 are tested.
Solvent Control Preparation Prepare a 1/10 dilution of methanol in sterile water.
Placement and culture of test solution 100 μl of the following solutions (pH 6, pH 7 and pH 8) are added to each cylinder.
-Methanol control (prepared for each strain at pH 7)
-0.05% solution B4,
-0.1% solution B3,
-0.5% solution B2.
Culture at 37 ° C. ± 1 ° C. for 24 hours (48 hours for Enterococcus hirae).
Determination of Minimum Inhibitory Concentration (MIC) After the test product has been diffused into the agar, the diameter of the inhibition as a result of inhibition of microbial growth is measured in millimeters using calipers.
The minimum bacteriostatic concentration (MIC) is given as the lowest concentration of product that prevents microbial growth.
If the highest concentration (500 μm / ml) is inactive, record this (> 500).
実施例1:ドデシルL−ラムノシドの合成
ピリジン100mlにL−ラムノース3gを含む溶液を調製する。
本方法に特有の中間ステップは、本方法の最初のステップの最後に得られる2,3,4−トリ−O−アセチル−ラムノピラノシルブロミド(5.817g)のジクロロメタン(120ml)溶液にドデカノール37mlを加え、微粉末状に粉砕したCaSO4(11.21g)、黄色粉末状HgO(5.647g)及びHgBr2(280mg)を加えるところにある。
Takeoらによる合成方法を合成が完了するまで実施し、ドデシルL−ラムノシドを得る。
合成の全体収率は54.9%である。
Example 1: Synthesis of dodecyl L-rhamnoside A solution containing 3 g of L-rhamnose in 100 ml of pyridine is prepared.
An intermediate step specific to the method is the addition of 2,3,4-tri-O-acetyl-rhamnopyranosyl bromide (5.817 g) in dichloromethane (120 ml) obtained at the end of the first step of the method. Add 37 ml of dodecanol and add CaSO 4 (11.21 g), yellow powdered HgO (5.647 g) and HgBr 2 (280 mg) ground to a fine powder.
The synthesis method by Takeo et al. Is carried out until the synthesis is completed to obtain dodecyl L-rhamnoside.
The overall yield of synthesis is 54.9%.
実施例2:オクチルL−フコシドの合成
L−フコース1.77gのピリジン70mlへの溶液を調製し、これに無水酢酸35mlを加える。
本合成方法に特有のステップは、本方法の最初のステップの最後に得られる2,3,4−トリ−O−アセチル−フコピラノシルブロミド(3.81g)のジクロロメタン(75ml)溶液にオクタノール17mlを加え、微粉末状に粉砕したCaSO4(7.34g)、黄色粉末状HgO(3.69g)及びHgBr2(183mg)を加えるところにある。
Takeoらによる合成方法を合成が完了するまで実施し、オクチルL−フコシドを得る。
合成の全体収率は58.6%である。
Example 2: Synthesis of octyl L-fucoside A solution of 1.77 g of L-fucose in 70 ml of pyridine is prepared, to which 35 ml of acetic anhydride is added.
The steps specific to this synthesis method are octanol in a solution of 2,3,4-tri-O-acetyl-fucopyranosyl bromide (3.81 g) obtained at the end of the first step of the method in dichloromethane (75 ml). 17 ml is added, and CaSO 4 (7.34 g), yellow powdered HgO (3.69 g) and HgBr 2 (183 mg) ground to a fine powder are added.
The synthesis method by Takeo et al. Is carried out until the synthesis is completed to obtain octyl L-fucoside.
The overall yield of synthesis is 58.6%.
実施例3:微生物増殖阻止活性
種々の菌株についてpH7で、アルキルグリコシド濃度を0.05重量%、0.1重量%及び0.5重量%として試験を実施した。
a)ラムノシドのアルキル誘導体の存在下における微生物増殖阻止活性
種々の微生物に対する化合物Fuc−1、Fuc−8及びFuc−12のそれぞれの活性を評価し、同じ濃度範囲で用いた陽性対照、KATHON(登録商標)の活性と比較する。
微生物の増殖に対する濃度の影響を評価するために、3種の濃度(0.05%、0.1%及び0.5%)を試験する。
結果を、高い濃度2種について添付の図1に示す。
それぞれの菌株についてのMICを、試験したそれぞれの分子について決定する(下記表1)。
a) Microbial growth inhibitory activity in the presence of alkyl derivatives of rhamnoside Each activity of the compounds Fuc-1, Fuc-8 and Fuc-12 against various microorganisms was evaluated and a positive control used in the same concentration range, KATHON (registered) To the activity of the trademark.
Three concentrations (0.05%, 0.1% and 0.5%) are tested to assess the effect of concentration on microbial growth.
The results are shown in the attached FIG. 1 for two high concentrations.
The MIC for each strain is determined for each molecule tested (Table 1 below).
結論
2種の化合物は、試験したすべての菌株に対して阻止活性を示す。
b)フコースのアルキル誘導体の存在下における微生物増殖阻止活性
種々の微生物に対する化合物Fuc−1、Fuc−8及びFuc−12のそれぞれの活性を評価し、同じ濃度範囲で用いた陽性対照、KATHON(登録商標)の活性と比較する。
微生物の増殖に対する濃度の影響を評価するために、3種の濃度を試験する。
結果は、添付の図2に示す。
それぞれの菌株についてのMICを、試験したそれぞれの分子について決定する(下記表2)。
b) Microbial growth inhibitory activity in the presence of alkyl derivatives of fucose The activity of each of the compounds Fuc-1, Fuc-8 and Fuc-12 against various microorganisms was evaluated and the positive control used in the same concentration range, KATHON (registered) To the activity of the trademark.
To assess the effect of concentration on microbial growth, three concentrations are tested.
The results are shown in the attached FIG.
The MIC for each strain is determined for each molecule tested (Table 2 below).
結論
フコースのアルキル誘導体は、前述の実施例のラムノース誘導体よりも、微生物に対して低い活性を示すように思われる。
さらに、これらの化合物はグラム(−)細菌に対しては活性を示さない。
一方、これらの分子は、フコースにグラフト化されたアルキル鎖の長さにかかわらず、グラム(+)細菌に対しては活性を示す。
実施例4:メチルマルトシドの合成
D−マルトース5gのピリジン220mlへの溶液を調製し、無水酢酸80ml(80ml)を加える。
本方法に特有の中間ステップは、2,2’,3,3’,4’,6,6’−ヘプタ−O−アセチル−α−D−マルトシルブロミド(2.05g)のジクロロメタン(16.5ml)溶液にメタノール5.5mlを加えるところにあり、メタノール5.5ml、微粉末状に粉砕したCaSO4(2g)、黄色粉末状HgO(1g)及びHgBr2(49mg)を加える。
本合成方法によりメチルβ−D−マルトシドが得られる。
合成の全体収率は75.4%である。
CONCLUSION The alkyl derivative of fucose appears to exhibit less activity against microorganisms than the rhamnose derivative of the previous example.
Furthermore, these compounds are not active against gram (-) bacteria.
On the other hand, these molecules are active against gram (+) bacteria, regardless of the length of the alkyl chain grafted to fucose.
Example 4: Synthesis of methyl maltoside A solution of 5 g of D-maltose in 220 ml of pyridine is prepared and 80 ml (80 ml) of acetic anhydride is added.
An intermediate step specific to this method is 2,2 ′, 3,3 ′, 4 ′, 6,6′-hepta-O-acetyl-α-D-maltosyl bromide (2.05 g) in dichloromethane (16. 5 ml) There is a place where 5.5 ml of methanol is added to the solution, and 5.5 ml of methanol, CaSO 4 (2 g) ground to a fine powder, HgO (1 g) in the form of yellow powder and HgBr 2 (49 mg) are added.
This synthesis method yields methyl β-D-maltoside.
The overall yield of synthesis is 75.4%.
実施例5:メチルマルトトリオシドの合成
D−マルトトリオース5gのピリジン150mlへの溶液(150ml)を調製し、無水酢酸50mlを加える。
本方法に特有の中間ステップは、本方法の最初のステップの最後に得られる2,2’,2’’,3,3’,3’’,4’,4’’,6,6’,6’’−デカ−O−アセチル−α−D−マルトトリオシルブロミド(2.878g)のジクロロメタン(20ml)溶液にメタノール6mlを加え、微粉末状に粉砕したCaSO4(2g)、黄色粉末状HgO(1g)及びHgBr2(49mg)を加えるところにある。
Takeoらによる合成方法を合成が完了するまで実施し、最終的にメチルβ−D−マルトトリオシドを得る。
合成法の全体収率は85%である。
Example 5: Synthesis of methyl maltotrioside A solution (150 ml) of 5 g D-maltotriose in 150 ml pyridine is prepared and 50 ml acetic anhydride is added.
The intermediate steps specific to the method are 2, 2 ′, 2 ″, 3, 3 ′, 3 ″, 4 ′, 4 ″, 6, 6 ′, obtained at the end of the first step of the method. 6 ml of methanol was added to a solution of 6 ″ -deca-O-acetyl-α-D-maltotriosyl bromide (2.878 g) in dichloromethane (20 ml) and pulverized into a fine powder, CaSO 4 (2 g), yellow powder Add HgO (1 g) and HgBr 2 (49 mg).
The synthesis method by Takeo et al. Is carried out until the synthesis is completed, and finally methyl β-D-maltotrioside is obtained.
The overall yield of the synthesis method is 85%.
実施例6:ドデシルマルトトリオシドの合成
D−マルトトリオース1.5g(2.97mmol)のピリジン50mlへの溶液を調製し、これに無水酢酸15mlを加える。
本合成方法に特有のステップは、本方法の最初のステップの最後に得られる2,2’,2’’,3,3’,3’’,4’,4’’,6,6’,6’’−デカ−O−アセチル−α−D−マルトトリオシルブロミド(2.93g)のジクロロメタン20ml溶液にドデカノール6.75mlを加え、微粉末状に粉砕したCaSO4(2.02g)、黄色粉末状HgO(1.017g)及びHgBr2(50.6mg)を加えるところにある。
Takeoらによる合成方法を合成が完了するまで実施し、最終的にドデルβ−D−マルトトリオシドを得る。
合成の全体収率は77.1%である。
Example 6: Synthesis of dodecyl maltotrioside A solution of 1.5 g (2.97 mmol) of D-maltotriose in 50 ml of pyridine is prepared, to which 15 ml of acetic anhydride is added.
The steps specific to the synthesis method are 2, 2 ′, 2 ″, 3, 3 ′, 3 ″, 4 ′, 4 ″, 6, 6 ′, obtained at the end of the first step of the method. To a 20 ml solution of 6 ″ -deca-O-acetyl-α-D-maltotriosyl bromide (2.93 g), 6.75 ml of dodecanol was added, and CaSO 4 (2.02 g) ground to a fine powder was yellow. Add powdered HgO (1.017 g) and HgBr 2 (50.6 mg).
The synthesis method by Takeo et al. Is carried out until the synthesis is completed, and finally dodel β-D-maltotrioside is obtained.
The overall yield of synthesis is 77.1%.
実施例7:メチルオリゴ糖(DPx−1)及びドデシルオリゴ糖(DPy−12)を含むアルキルグリコシドの2成分混合物の存在下における微生物増殖阻止活性(x=2又は3、y=2又は3、及びx=y又はx≠y)
下記のアルキルグリコシドA、B、C、Dの混合物の活性を種々の微生物について評価する。
A=DP2−1 + DP2−12(1:1)
B=DP3−1 + DP3−12(1:1)
C=DP2−1 + DP3−12(1:1)
D=DP2−12 + DP3−1(1:1)
微生物の増殖に対するこれらの混合物の影響を評価するために、2種の濃度の混合物を試験する。
結果を添付の図3に示す。
Example 7: Microbial growth inhibitory activity (x = 2 or 3, y = 2 or 3, in the presence of a binary mixture of alkyl glycosides containing methyl oligosaccharide (DPx-1) and dodecyl oligosaccharide (DPy-12) And x = y or x ≠ y)
The activity of the following mixture of alkyl glycosides A, B, C, D is evaluated for various microorganisms.
A = DP2-1 + DP2-12 (1: 1)
B = DP3-1 + DP3-12 (1: 1)
C = DP2-1 + DP3-12 (1: 1)
D = DP2-12 + DP3-1 (1: 1)
To assess the effect of these mixtures on microbial growth, two concentrations of the mixture are tested.
The results are shown in the attached FIG.
結論
試験した混合物は、グラム(−)細菌に対しては顕著な活性を示さない。
しかし、他の微生物に対する濃度0.5%以上での活性は、これらの混合物に防腐剤としての相補的な性質を付与し、化粧品用組成における使用を特に有利なものにしている。
この活性により、本発明の化粧品用組成物における防腐剤組成物の調整が可能になる。
Conclusion The tested mixture does not show significant activity against gram (-) bacteria.
However, activity at concentrations of 0.5% or more against other microorganisms imparts complementary properties as preservatives to these mixtures, making them particularly advantageous for use in cosmetic compositions.
This activity makes it possible to adjust the preservative composition in the cosmetic composition of the present invention.
実施例8:微生物増殖阻止剤として本発明による2種のアルキルグリコシドの混合物を含む抗老化エマルジョンクリーム
百分率は、最終組成物に対する重量として表される。
− Centella asiaticaの植物抽出物 0.1
− 界面活性剤(Arlacel(登録商標)165VP) 5
− セチルアルコール 95% 1
− ステアリルアルコール 1
− 蜜ろう 1.5
− オイル(Perleam(登録商標)) 8.5
− トリカプレート/カプリレートグリセリド 3
− シリコーンオイル(ジメチコーン 100CS) 1
− ポリマー(Keltrol(登録商標)) 0.35
− 水酸化ナトリウム 0.04
− EDTA四ナトリウム塩粉末 0.1
− ドデシルL−ラムノシド 0.5
− 水 100までの適量
Example 8: Anti-aging emulsion cream comprising a mixture of two alkyl glycosides according to the invention as a microbial growth inhibitor The percentage is expressed as a weight relative to the final composition.
-Plant extract of Centella asiatica 0.1
-Surfactant (Arlacel® 165VP) 5
-Cetyl alcohol 95% 1
-
-Beeswax 1.5
-Oil (Perleam®) 8.5
-Tricaprate / Caprylate glycerides 3
-Silicone oil (Dimethicone 100CS) 1
-Polymer (Keltrol (R)) 0.35
-Sodium hydroxide 0.04
-EDTA tetrasodium salt powder 0.1
-Dodecyl L-rhamnoside 0.5
-Appropriate amount of water up to 100
実施例9:微生物増殖阻止剤として本発明による2種のアルキルグリコシドの混合物を含むファンデーション
百分率は、最終組成物に対する重量として表す。
− 雲母 31
− 二酸化チタン 22.4
− タルク 11
− 無水シリカ 6
− Nylon−12 8
− メトキシケイ皮酸オクチル 7
− メチルフェニルポリシロキサン 2.5
− ステアリン酸 2
− ステアリン酸マグネシウム 1.5
− 着色剤(酸化鉄) 2.5
− フェニルトリメチコーン 2
− グリセリン 2
− メチルβ−D−マルトシド 0.5
− ドデシルβ−D−マルトトリオシド 0.5
− 香料、着色剤、中和剤 適量
Example 9: Foundation comprising a mixture of two alkyl glycosides according to the invention as a microbial growth inhibitor
Percentages are expressed as weight relative to the final composition.
-Mica 31
-Titanium dioxide 22.4
-Talc 11
-Anhydrous silica 6
-Nylon-12 8
-Octyl methoxycinnamate 7
-Methylphenylpolysiloxane 2.5
-Stearic acid 2
-Magnesium stearate 1.5
-Colorant (iron oxide) 2.5
-Phenyltrimethicone 2
-Glycerin 2
-Methyl β-D-maltoside 0.5
-Dodecyl β-D-maltotrioside 0.5
-Perfume, coloring agent, neutralizing agent
実施例10:微生物増殖阻止剤として本発明による4種のアルキルグリコシドの混合物を含むシャンプー
百分率は、最終組成物に対する重量として表す。
− ポリアクリル酸ナトリウム架橋体 4
− ラウレス硫酸ナトリウム 11.9
− コカミドプロピルベタイン 2.5
− PEG−9 ココグリセリド 2.5
− ココイル加水分解小麦タンパク質ナトリウム 0.9
− メチルβ−D−マルトシド 0.25
− メチルβ−D−マルトトリオシド 0.25
− ドデシルβ−D−マルトシド 0.25
− ドデシルβ−D−マルトトリオシド 0.25
− 顔料、香料、抗酸化剤 適量
− 純水 100までの適量
Example 10: Shampoo containing a mixture of four alkyl glycosides according to the invention as a microbial growth inhibitor The percentage is expressed as a weight relative to the final composition.
-Cross-linked sodium polyacrylate 4
-Sodium laureth sulfate 11.9
-Cocamidopropyl betaine 2.5
-PEG-9 cocoglyceride 2.5
-Sodium cocoyl hydrolyzed wheat protein 0.9
-Methyl β-D-maltoside 0.25
-Methyl β-D-maltotrioside 0.25
-Dodecyl β-D-maltoside 0.25
-Dodecyl β-D-maltotrioside 0.25
-Pigments, fragrances, antioxidants appropriate amount-Pure water Appropriate amounts up to 100
実施例8〜10の上述の本発明による組成物は、1種又は複数のアルキルグリコシドによって微生物汚染から保護され、したがって微生物増殖阻止を目的とした他の剤、特にパラベン族の防腐剤を含まないことが注目されるであろう。 The above-described compositions according to the invention of Examples 8 to 10 are protected from microbial contamination by one or more alkyl glycosides and are therefore free of other agents intended to prevent microbial growth, in particular parabens preservatives. It will be noted.
Claims (31)
或いは、少なくとも2種のアルキルグリコシドの混合物が
上記定義の一般式(I)の化合物から選択される少なくとも1種の化合物を含む混合物;
一般式(II)(S2)−O−R2(式中、(S2)は1個の糖単位又は一連の2〜8個の同一若しくは異なる糖単位で形成されるオリゴ糖であり、(R2)は1〜6個の炭素原子を含むアルキル基である)の化合物から選択される少なくとも1種の化合物及び一般式(III)(S3)−O−R3(式中、(S3)は1個の糖単位又は一連の2〜8個の同一若しくは異なる糖単位で形成されるオリゴ糖であり、R3は8〜24個の炭素原子を含むアルキル基である)の化合物から選択される少なくとも1種の化合物を含む混合物
から選択されることを特徴とする請求項1に記載の剤。 The alkyl glycoside is represented by the general formula (I) (S 1 ) —O—R 1 (wherein (S 1 ) is deoxyaldhexose and R 1 is an alkyl group containing 1 to 24 carbon atoms) Selected from the compounds of
Alternatively, a mixture wherein the mixture of at least two alkyl glycosides comprises at least one compound selected from the compounds of general formula (I) as defined above;
General formula (II) (S 2 ) —O—R 2 , wherein (S 2 ) is an oligosaccharide formed with one sugar unit or a series of 2-8 identical or different sugar units; (R 2 ) is at least one compound selected from compounds of the formula (III) (S 3 ) —O—R 3 (wherein (R 2 ) is an alkyl group containing 1 to 6 carbon atoms) S 3 ) is an oligosaccharide formed by one sugar unit or a series of 2 to 8 identical or different sugar units, and R 3 is an alkyl group containing 8 to 24 carbon atoms) The agent according to claim 1, wherein the agent is selected from a mixture comprising at least one compound selected from the group consisting of:
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US10874700B2 (en) | 2016-03-31 | 2020-12-29 | Gojo Industries, Inc. | Sanitizer composition with probiotic/prebiotic active ingredient |
US11633451B2 (en) | 2016-03-31 | 2023-04-25 | Gojo Industries, Inc. | Antimicrobial peptide stimulating cleansing composition |
US11998575B2 (en) | 2016-03-31 | 2024-06-04 | Gojo Industries, Inc. | Sanitizer composition with probiotic/prebiotic active ingredient |
US11564879B2 (en) | 2016-11-23 | 2023-01-31 | Gojo Industries, Inc. | Sanitizer composition with probiotic/prebiotic active ingredient |
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FR2929509A1 (en) | 2009-10-09 |
JP5652774B2 (en) | 2015-01-14 |
DE102009015608A1 (en) | 2009-11-05 |
JP2015107965A (en) | 2015-06-11 |
JP6106879B2 (en) | 2017-04-05 |
US20130142742A1 (en) | 2013-06-06 |
FR2929509B1 (en) | 2011-01-21 |
US20090306011A1 (en) | 2009-12-10 |
US9232793B2 (en) | 2016-01-12 |
US8377892B2 (en) | 2013-02-19 |
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